Local-Approved Itineraries
Proven Trip Plans for First-Timers to Paradise
Written by a Local Expert
Leilani AkoLocal-Approved Itineraries for First-Timers
These sample itineraries are designed to give first-time visitors a taste of each island's unique character while allowing time to truly connect with the ʻāina (land) and local culture. Remember, the best trips to Hawaiʻi balance must-see sights with spontaneous discovery.
These itineraries blend iconic sights with local-approved experiences and allow for the spontaneous magic that makes a trip to Hawaiʻi special. Use them as flexible templates, not rigid schedules.
🌺 The 7-Day Oʻahu "Best of Both Worlds" Itinerary
This plan is perfect for first-timers who want to experience Oʻahu's famous history and city life alongside its stunning natural beauty.
Days 1-3: Honolulu & The South Shore
Arrive at Honolulu International Airport (HNL), pick up your rental car (or plan to use rideshare/TheBus in town), and check into your Waikīkī accommodation.
Day 1
Settle in, take a walk along Waikīkī Beach, and enjoy the sunset.
Day 2
Morning at Pearl Harbor (book USS Arizona Memorial tickets online in advance). Afternoon: ʻIolani Palace and King Kamehameha I statue.
Day 3
Hike Diamond Head in the morning (reservations required). Afternoon: explore local food scene in Kapahulu or Kaimukī.
Days 4-5: The Windward Coast & North Shore
Day 4
Drive the scenic windward (east) coast. Stop at Makapuʻu Point Lighthouse Trail and relax on Waimānalo Beach.
Day 5
Head to the North Shore. Explore Haleʻiwa, watch surfers at Waimea Bay or Sunset Beach, sample garlic shrimp from a food truck.
Days 6-7: Leeward Exploration & Departure
Day 6
Explore Leeward (west) coast beaches or adventure activities at Coral Crater Adventure Park. Enjoy a memorable dinner.
Day 7
One last dip in the ocean before heading to HNL for your departure.
🌴 The 10-Day Maui & Kauaʻi "Adventure & Relaxation" Itinerary
This itinerary is for those who want to pair Maui's upscale adventure with Kauaʻi's raw, natural beauty.
Days 1-5: The Magic of Maui
Arrive at Kahului Airport (OGG). Stay in either West Maui (Kāʻanapali) for a resort feel or South Maui (Wailea/Kīhei) for great beaches and condos.
Day 1
Arrive, check in, and relax.
Day 2
Drive the Road to Hāna. Start early and focus on key stops like Waiʻānapanapa State Park (reservations required).
Day 3
Experience Haleakalā National Park. Opt for sunset to avoid crowds and 3 AM wakeup.
Day 4
Ocean day. Snorkel trip to Molokini Crater or explore reefs at Kahekili Beach.
Day 5
Explore Upcountry towns like Makawao and Kula, or visit Aliʻi Kula Lavender Farm.
Days 6-10: The Untamed Beauty of Kauaʻi
Take a morning flight from OGG to Līhuʻe (LIH).
Day 6
Check into accommodation on South Shore (Poʻipū) or North Shore (Princeville/Hanalei).
Day 7
Splurge on Nāpali Coast helicopter or boat tour. This is the only way to truly grasp the scale of these cliffs.
Day 8
Drive to Waimea Canyon State Park, the "Grand Canyon of the Pacific."
Day 9
Relax at Poʻipū Beach or kayak the peaceful Hanalei River.
Day 10
Enjoy a final Hawaiian sunrise before departing from LIH.
🌋 The 14-Day Oʻahu & Big Island "Culture & Creation" Itinerary
This two-week journey combines the rich history of Oʻahu with the raw, elemental power of the Big Island.
Days 1-6: Oʻahu's Cultural Core
Follow a more relaxed version of the 7-day Oʻahu itinerary. Use the extra time to delve deeper into culture at the Bishop Museum, Hawaiʻi's premier natural and cultural history institution, or explore the Honolulu Museum of Art.
Days 7-14: The Big Island's Land of Fire and Water
Fly from HNL to Kona (KOA).
Days 7-10 (Kona Side)
Stay on the sunny west side:
- • Tour a Kona coffee farm to learn the bean-to-cup process
- • Snorkel at Kealakekua Bay or Two Step for clear water and dolphins
- • Experience the once-in-a-lifetime manta ray night snorkel
Days 11-14 (Hilo Side & Departure)
Drive across the island to the Hilo side:
- • Dedicate a full day and night to Hawaiʻi Volcanoes National Park
- • Stay in nearby Volcano Village to see dramatic crater glow after dark
- • Explore Hilo area's waterfalls like ʻAkaka Falls and Rainbow Falls
- • Visit historic downtown before departing from Hilo (ITO) or driving back to Kona (KOA)
📋 Itinerary Overview
🎟️ Key Reservations
- USS Arizona Memorial (recreation.gov)
- Diamond Head State Monument
- Waiʻānapanapa State Park
- Haleakalā National Park (sunrise)
🚗 Transportation Tips
🎒 Packing Essentials
- Reef-safe sunscreen
- Reusable water bottle
- Waterproof phone case
- Light rain jacket
- Hiking shoes (clean)
💰 Budget Estimates
Ready to Budget Your Trip?
Now that you have your itinerary planned, let's make sure you budget wisely and pack properly for your Hawaiian adventure.